NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.1
Volume:	261.486
LogP:	2.968
LogD:	1.659
LogS:	-2.63
# Rotatable Bonds:	3
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.253
Synthetic Accessibility Score:	3.079
Fsp3:	0.214
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.892
MDCK Permeability:	2.0220897567924112e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	99.81966400146484%
Volume Distribution (VD):	0.217
Pgp-substrate:	2.0192999839782715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.775
CYP1A2-substrate:	0.891
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.192
CYP2C9-inhibitor:	0.11
CYP2C9-substrate:	0.54
CYP2D6-inhibitor:	0.374
CYP2D6-substrate:	0.503
CYP3A4-inhibitor:	0.135
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	10.781
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.635
Drug-inuced Liver Injury (DILI):	0.539
AMES Toxicity:	0.662
Rat Oral Acute Toxicity:	0.229
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.958
Carcinogencity:	0.541
Eye Corrosion:	0.05
Eye Irritation:	0.925
Respiratory Toxicity:	0.894

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC123714

Natural Product ID:	NPC123714
*Common Name:**	Sohirnone B
IUPAC Name:	(2E,4E)-1-(2,4,5-trihydroxy-3,6-dimethylphenyl)hexa-2,4-dien-1-one
Synonyms:
Standard InCHIKey:	HTOGTGFTMLQGFO-YTXTXJHMSA-N
Standard InCHI:	InChI=1S/C14H16O4/c1-4-5-6-7-10(15)11-8(2)13(17)14(18)9(3)12(11)16/h4-7,16-18H,1-3H3/b5-4+,7-6+
SMILES:	C/C=C/C=C/C(=O)c1c(C)c(c(c(C)c1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509797
PubChem CID:	11413968
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001310] Benzenetriols and derivatives [CHEMONTID:0000380] Hydroxyquinols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32492	penicillium notatum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974609]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	12.0	mm	PMID[530065]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	12.0	mm	PMID[530065]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	13.0	mm	PMID[530065]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC123714 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	1630
0.2-0.3	4161
0.3-0.4	11256
0.4-0.5	8068
0.5-0.6	5390
0.6-0.7	6647
0.7-0.8	4732
0.8-0.85	376
0.85-0.9	49
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9071	High Similarity	NPC238629
0.9065	High Similarity	NPC92079
0.9044	High Similarity	NPC14377
0.8913	High Similarity	NPC290030
0.8857	High Similarity	NPC203063
0.8841	High Similarity	NPC194764
0.8841	High Similarity	NPC264112
0.8841	High Similarity	NPC65005
0.8786	High Similarity	NPC143438
0.8786	High Similarity	NPC472903
0.8732	High Similarity	NPC291078
0.8714	High Similarity	NPC61398
0.8714	High Similarity	NPC416
0.8696	High Similarity	NPC282780
0.8696	High Similarity	NPC166480
0.8686	High Similarity	NPC135801
0.8662	High Similarity	NPC472904
0.8652	High Similarity	NPC242994
0.8652	High Similarity	NPC138099
0.8643	High Similarity	NPC53414
0.8643	High Similarity	NPC147418
0.8643	High Similarity	NPC53206
0.8639	High Similarity	NPC48949
0.8633	High Similarity	NPC129752
0.8633	High Similarity	NPC258502
0.863	High Similarity	NPC471907
0.8613	High Similarity	NPC469526
0.8613	High Similarity	NPC34070
0.8592	High Similarity	NPC169452
0.8592	High Similarity	NPC181560
0.8581	High Similarity	NPC35
0.8571	High Similarity	NPC471690
0.8571	High Similarity	NPC254847
0.854	High Similarity	NPC117609
0.854	High Similarity	NPC26697
0.854	High Similarity	NPC233056
0.8531	High Similarity	NPC187843
0.8521	High Similarity	NPC162939
0.8511	High Similarity	NPC471905
0.8497	Intermediate Similarity	NPC311740
0.8493	Intermediate Similarity	NPC476535
0.8489	Intermediate Similarity	NPC48036
0.8489	Intermediate Similarity	NPC267205
0.8489	Intermediate Similarity	NPC37299
0.8489	Intermediate Similarity	NPC180261
0.8483	Intermediate Similarity	NPC244691
0.8472	Intermediate Similarity	NPC193555
0.8472	Intermediate Similarity	NPC314271
0.8451	Intermediate Similarity	NPC206207
0.8444	Intermediate Similarity	NPC477454
0.8442	Intermediate Similarity	NPC470694
0.844	Intermediate Similarity	NPC118919
0.844	Intermediate Similarity	NPC223836
0.844	Intermediate Similarity	NPC191976
0.8431	Intermediate Similarity	NPC119224
0.8431	Intermediate Similarity	NPC84571
0.8429	Intermediate Similarity	NPC474519
0.8429	Intermediate Similarity	NPC44437
0.8421	Intermediate Similarity	NPC303737
0.8406	Intermediate Similarity	NPC62219
0.8406	Intermediate Similarity	NPC244441
0.84	Intermediate Similarity	NPC161778
0.8392	Intermediate Similarity	NPC471819
0.8392	Intermediate Similarity	NPC190457
0.8389	Intermediate Similarity	NPC280295
0.8387	Intermediate Similarity	NPC207690
0.8387	Intermediate Similarity	NPC101769
0.8382	Intermediate Similarity	NPC473691
0.8369	Intermediate Similarity	NPC290803
0.8369	Intermediate Similarity	NPC161632
0.8366	Intermediate Similarity	NPC45846
0.8358	Intermediate Similarity	NPC309765
0.8357	Intermediate Similarity	NPC294226
0.8356	Intermediate Similarity	NPC10764
0.8355	Intermediate Similarity	NPC142339
0.8345	Intermediate Similarity	NPC135524
0.8345	Intermediate Similarity	NPC474961
0.8344	Intermediate Similarity	NPC107109
0.8344	Intermediate Similarity	NPC93552
0.8344	Intermediate Similarity	NPC273248
0.8333	Intermediate Similarity	NPC187690
0.8333	Intermediate Similarity	NPC471853
0.8333	Intermediate Similarity	NPC92624
0.8323	Intermediate Similarity	NPC329760
0.8322	Intermediate Similarity	NPC175552
0.8322	Intermediate Similarity	NPC230811
0.8322	Intermediate Similarity	NPC141368
0.8321	Intermediate Similarity	NPC107672
0.8321	Intermediate Similarity	NPC214620
0.8312	Intermediate Similarity	NPC235018
0.8312	Intermediate Similarity	NPC45146
0.8311	Intermediate Similarity	NPC251188
0.8301	Intermediate Similarity	NPC37543
0.8301	Intermediate Similarity	NPC178976
0.8301	Intermediate Similarity	NPC199463
0.8301	Intermediate Similarity	NPC236796
0.8289	Intermediate Similarity	NPC472048
0.8284	Intermediate Similarity	NPC215392
0.828	Intermediate Similarity	NPC37870
0.8278	Intermediate Similarity	NPC149889
0.8278	Intermediate Similarity	NPC312338
0.8276	Intermediate Similarity	NPC246638
0.8276	Intermediate Similarity	NPC290550
0.8276	Intermediate Similarity	NPC305845
0.8276	Intermediate Similarity	NPC204045
0.8273	Intermediate Similarity	NPC17840
0.8273	Intermediate Similarity	NPC247477
0.8273	Intermediate Similarity	NPC259942
0.8269	Intermediate Similarity	NPC236132
0.8269	Intermediate Similarity	NPC270837
0.8267	Intermediate Similarity	NPC474191
0.8267	Intermediate Similarity	NPC476532
0.8258	Intermediate Similarity	NPC32694
0.8255	Intermediate Similarity	NPC287395
0.8255	Intermediate Similarity	NPC183655
0.8255	Intermediate Similarity	NPC15329
0.8255	Intermediate Similarity	NPC131451
0.8255	Intermediate Similarity	NPC112816
0.8248	Intermediate Similarity	NPC472047
0.8248	Intermediate Similarity	NPC8745
0.8247	Intermediate Similarity	NPC172770
0.8247	Intermediate Similarity	NPC185258
0.8247	Intermediate Similarity	NPC100123
0.8239	Intermediate Similarity	NPC278375
0.8239	Intermediate Similarity	NPC72918
0.8235	Intermediate Similarity	NPC77807
0.8235	Intermediate Similarity	NPC470762
0.8235	Intermediate Similarity	NPC14561
0.8235	Intermediate Similarity	NPC474167
0.8235	Intermediate Similarity	NPC25850
0.8235	Intermediate Similarity	NPC5379
0.8235	Intermediate Similarity	NPC276815
0.8231	Intermediate Similarity	NPC193703
0.8231	Intermediate Similarity	NPC21599
0.8231	Intermediate Similarity	NPC471906
0.8227	Intermediate Similarity	NPC111845
0.8227	Intermediate Similarity	NPC138472
0.8224	Intermediate Similarity	NPC477048
0.8224	Intermediate Similarity	NPC96160
0.8224	Intermediate Similarity	NPC477047
0.8224	Intermediate Similarity	NPC89474
0.8224	Intermediate Similarity	NPC4331
0.8222	Intermediate Similarity	NPC91105
0.8219	Intermediate Similarity	NPC73061
0.8217	Intermediate Similarity	NPC26386
0.8214	Intermediate Similarity	NPC205992
0.8212	Intermediate Similarity	NPC202157
0.8209	Intermediate Similarity	NPC472046
0.8205	Intermediate Similarity	NPC294965
0.8201	Intermediate Similarity	NPC474998
0.8201	Intermediate Similarity	NPC109123
0.8201	Intermediate Similarity	NPC278928
0.82	Intermediate Similarity	NPC102003
0.82	Intermediate Similarity	NPC134293
0.82	Intermediate Similarity	NPC92722
0.8194	Intermediate Similarity	NPC80375
0.8194	Intermediate Similarity	NPC228785
0.8194	Intermediate Similarity	NPC320359
0.8194	Intermediate Similarity	NPC56085
0.8194	Intermediate Similarity	NPC14353
0.8188	Intermediate Similarity	NPC162612
0.8188	Intermediate Similarity	NPC72158
0.8188	Intermediate Similarity	NPC30501
0.8188	Intermediate Similarity	NPC169250
0.8188	Intermediate Similarity	NPC100067
0.8188	Intermediate Similarity	NPC23126
0.8188	Intermediate Similarity	NPC103356
0.8188	Intermediate Similarity	NPC266689
0.8188	Intermediate Similarity	NPC137296
0.8188	Intermediate Similarity	NPC98254
0.8188	Intermediate Similarity	NPC105157
0.8188	Intermediate Similarity	NPC83572
0.8188	Intermediate Similarity	NPC190043
0.8188	Intermediate Similarity	NPC37709
0.8182	Intermediate Similarity	NPC315275
0.8182	Intermediate Similarity	NPC158481
0.8182	Intermediate Similarity	NPC179732
0.8182	Intermediate Similarity	NPC79053
0.8182	Intermediate Similarity	NPC283301
0.8176	Intermediate Similarity	NPC34482
0.8175	Intermediate Similarity	NPC10926
0.8175	Intermediate Similarity	NPC475733
0.8175	Intermediate Similarity	NPC201728
0.8175	Intermediate Similarity	NPC262671
0.817	Intermediate Similarity	NPC113906
0.817	Intermediate Similarity	NPC134287
0.817	Intermediate Similarity	NPC39184
0.817	Intermediate Similarity	NPC130589
0.8169	Intermediate Similarity	NPC474394
0.8163	Intermediate Similarity	NPC313047
0.8163	Intermediate Similarity	NPC295712
0.8163	Intermediate Similarity	NPC474203
0.8163	Intermediate Similarity	NPC287722
0.8163	Intermediate Similarity	NPC451542
0.8162	Intermediate Similarity	NPC472029
0.8162	Intermediate Similarity	NPC65761
0.8158	Intermediate Similarity	NPC476533
0.8156	Intermediate Similarity	NPC175738
0.8156	Intermediate Similarity	NPC88864
0.8153	Intermediate Similarity	NPC23298

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC123714 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	1069
0.2-0.3	1941
0.3-0.4	3027
0.4-0.5	1642
0.5-0.6	802
0.6-0.7	255
0.7-0.8	51
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8841	High Similarity	NPD651	Clinical (unspecified phase)
0.8686	High Similarity	NPD943	Approved
0.8571	High Similarity	NPD1509	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD7390	Discontinued
0.8054	Intermediate Similarity	NPD2532	Approved
0.8054	Intermediate Similarity	NPD2534	Approved
0.8054	Intermediate Similarity	NPD2533	Approved
0.7956	Intermediate Similarity	NPD9269	Phase 2
0.7933	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD2801	Approved
0.7871	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6232	Discontinued
0.7826	Intermediate Similarity	NPD7473	Discontinued
0.7786	Intermediate Similarity	NPD1470	Approved
0.7755	Intermediate Similarity	NPD5408	Approved
0.7755	Intermediate Similarity	NPD5406	Approved
0.7755	Intermediate Similarity	NPD5404	Approved
0.7755	Intermediate Similarity	NPD5405	Approved
0.7748	Intermediate Similarity	NPD1511	Approved
0.7724	Intermediate Similarity	NPD230	Phase 1
0.7664	Intermediate Similarity	NPD9268	Approved
0.7647	Intermediate Similarity	NPD1512	Approved
0.7626	Intermediate Similarity	NPD1201	Approved
0.758	Intermediate Similarity	NPD1934	Approved
0.7551	Intermediate Similarity	NPD1607	Approved
0.7547	Intermediate Similarity	NPD3882	Suspended
0.7483	Intermediate Similarity	NPD2800	Approved
0.7445	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1240	Approved
0.741	Intermediate Similarity	NPD5844	Phase 1
0.7407	Intermediate Similarity	NPD5494	Approved
0.74	Intermediate Similarity	NPD2935	Discontinued
0.7355	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4380	Phase 2
0.7338	Intermediate Similarity	NPD3300	Phase 2
0.7333	Intermediate Similarity	NPD1510	Phase 2
0.7317	Intermediate Similarity	NPD5711	Approved
0.7317	Intermediate Similarity	NPD5710	Approved
0.7312	Intermediate Similarity	NPD7819	Suspended
0.7286	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6959	Discontinued
0.7246	Intermediate Similarity	NPD3818	Discontinued
0.7244	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6166	Phase 2
0.7229	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1465	Phase 2
0.72	Intermediate Similarity	NPD6651	Approved
0.7184	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1164	Approved
0.7152	Intermediate Similarity	NPD1247	Approved
0.7124	Intermediate Similarity	NPD2346	Discontinued
0.7117	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1549	Phase 2
0.7073	Intermediate Similarity	NPD7075	Discontinued
0.7063	Intermediate Similarity	NPD3226	Approved
0.7059	Intermediate Similarity	NPD7074	Phase 3
0.7055	Intermediate Similarity	NPD3817	Phase 2
0.7035	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD447	Suspended
0.7019	Intermediate Similarity	NPD6599	Discontinued
0.7013	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7054	Approved
0.6994	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8150	Discontinued
0.6959	Remote Similarity	NPD7472	Approved
0.6959	Remote Similarity	NPD9494	Approved
0.6951	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6535	Approved
0.6927	Remote Similarity	NPD6534	Approved
0.6919	Remote Similarity	NPD6797	Phase 2
0.6879	Remote Similarity	NPD3750	Approved
0.6879	Remote Similarity	NPD7251	Discontinued
0.6879	Remote Similarity	NPD6559	Discontinued
0.6871	Remote Similarity	NPD7411	Suspended
0.6867	Remote Similarity	NPD3749	Approved
0.6867	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD9266	Approved
0.6861	Remote Similarity	NPD74	Approved
0.6855	Remote Similarity	NPD6799	Approved
0.6839	Remote Similarity	NPD2796	Approved
0.6835	Remote Similarity	NPD6190	Approved
0.6831	Remote Similarity	NPD9493	Approved
0.6829	Remote Similarity	NPD6801	Discontinued
0.6826	Remote Similarity	NPD919	Approved
0.6813	Remote Similarity	NPD7700	Phase 2
0.6813	Remote Similarity	NPD7699	Phase 2
0.6812	Remote Similarity	NPD4750	Phase 3
0.6802	Remote Similarity	NPD6020	Phase 2
0.6791	Remote Similarity	NPD846	Approved
0.6791	Remote Similarity	NPD940	Approved
0.6788	Remote Similarity	NPD9267	Approved
0.6788	Remote Similarity	NPD9264	Approved
0.6788	Remote Similarity	NPD9263	Approved
0.6788	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7635	Approved
0.6774	Remote Similarity	NPD2799	Discontinued
0.6772	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8166	Discontinued
0.6765	Remote Similarity	NPD3926	Phase 2
0.6759	Remote Similarity	NPD3019	Approved
0.6759	Remote Similarity	NPD2932	Approved
0.6747	Remote Similarity	NPD5402	Approved
0.6743	Remote Similarity	NPD7808	Phase 3
0.6739	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6777	Approved
0.6739	Remote Similarity	NPD6776	Approved
0.6739	Remote Similarity	NPD6778	Approved
0.6739	Remote Similarity	NPD6779	Approved
0.6739	Remote Similarity	NPD6780	Approved
0.6739	Remote Similarity	NPD6781	Approved
0.6739	Remote Similarity	NPD6782	Approved
0.6731	Remote Similarity	NPD1551	Phase 2
0.6731	Remote Similarity	NPD6099	Approved
0.6731	Remote Similarity	NPD6100	Approved
0.6728	Remote Similarity	NPD920	Approved
0.6726	Remote Similarity	NPD6234	Discontinued
0.6725	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD1243	Approved
0.6707	Remote Similarity	NPD7768	Phase 2
0.6705	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3022	Approved
0.6691	Remote Similarity	NPD3021	Approved
0.6688	Remote Similarity	NPD2344	Approved
0.6685	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6213	Phase 3
0.6685	Remote Similarity	NPD6212	Phase 3
0.6667	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD7435	Discontinued
0.6629	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD37	Approved
0.6626	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD9545	Approved
0.6605	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD411	Approved
0.6601	Remote Similarity	NPD3764	Approved
0.6601	Remote Similarity	NPD2313	Discontinued
0.6591	Remote Similarity	NPD5031	Approved
0.6591	Remote Similarity	NPD5029	Approved
0.6591	Remote Similarity	NPD5027	Approved
0.6579	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD9281	Approved
0.6562	Remote Similarity	NPD4628	Phase 3
0.6561	Remote Similarity	NPD3748	Approved
0.6554	Remote Similarity	NPD5028	Approved
0.6554	Remote Similarity	NPD5026	Approved
0.6554	Remote Similarity	NPD5034	Approved
0.6554	Remote Similarity	NPD4954	Approved
0.6554	Remote Similarity	NPD36	Approved
0.6554	Remote Similarity	NPD4955	Approved
0.6545	Remote Similarity	NPD8151	Discontinued
0.6543	Remote Similarity	NPD7696	Phase 3
0.6543	Remote Similarity	NPD7698	Approved
0.6543	Remote Similarity	NPD7697	Approved
0.6536	Remote Similarity	NPD3027	Phase 3
0.6534	Remote Similarity	NPD5953	Discontinued
0.6531	Remote Similarity	NPD4626	Approved
0.6522	Remote Similarity	NPD2309	Approved
0.6517	Remote Similarity	NPD8312	Approved
0.6517	Remote Similarity	NPD8313	Approved
0.6514	Remote Similarity	NPD7286	Phase 2
0.6513	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.651	Remote Similarity	NPD9717	Approved
0.6509	Remote Similarity	NPD4965	Approved
0.6509	Remote Similarity	NPD4966	Approved
0.6509	Remote Similarity	NPD4967	Phase 2
0.6508	Remote Similarity	NPD7871	Phase 2
0.6508	Remote Similarity	NPD7870	Phase 2
0.65	Remote Similarity	NPD5037	Approved
0.65	Remote Similarity	NPD5038	Approved
0.65	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5030	Phase 2
0.6496	Remote Similarity	NPD9261	Approved
0.6492	Remote Similarity	NPD7701	Phase 2
0.6489	Remote Similarity	NPD6823	Phase 2
0.6481	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD1471	Phase 3
0.6474	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1651	Approved
0.6461	Remote Similarity	NPD5032	Approved
0.646	Remote Similarity	NPD7003	Approved
0.6458	Remote Similarity	NPD5951	Approved
0.6457	Remote Similarity	NPD3751	Discontinued
0.6457	Remote Similarity	NPD7228	Approved
0.6447	Remote Similarity	NPD257	Approved
0.6447	Remote Similarity	NPD258	Approved
0.6447	Remote Similarity	NPD2798	Approved
0.6446	Remote Similarity	NPD7458	Discontinued
0.6444	Remote Similarity	NPD5036	Approved
0.6429	Remote Similarity	NPD4625	Phase 3
0.6425	Remote Similarity	NPD5035	Approved
0.6425	Remote Similarity	NPD7875	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data